Chesterfield Gambit Share definition Flag Whenever your friend does something so fucking clutch that you make up a bullshit name for it so that it seems like it was planned. “Dude, Brian just shot my grandma!” “Ain’t no way bro just pulled the Chesterfield Gambit!” Chesterfield Gambit by A Real, Genuine Human November 1, 2023 Get the Chesterfield Gambit mug.